2-AMino-3-benzyloxypyridine-5-boronic acid pinacol ester synthesis

Yield:756520-57-7 97%

Reaction Conditions:

with potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in dichloromethane;dimethyl sulfoxide at 80; for 16 h;

Steps:

I.488.1

To a solution of 3-BENZYLOXY-5-BROMO-PYRIDIN-2-YLAMINE (1 G, 3. 58 MMOL) in DIMETHYLSULFOXIDE (7 mL) was added sequentially bis (pinacolato) diborane (1. 0 G, 3. 94 MMOL), potassium acetate (1. 05 G, 10. 7 MMOL) [1, 1'-bis (diphenylphosphino) ferrocine] DICHLOROPALLADIUM (II), COMPLEX with dichloromethane (1 : 1) (146 mg, 0. 18 MMOL). The mixture was heated to 80 C for 16 hr and then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (50 mL) and filtered. The filtrate was washed with water (2X50 mL) and dried over magnesium sulfate. Concentration in vacuo yielded the crude boronate as a brown solid (1. 13 G, 97%). 1H NMR (CDC13) 1. 32 (s, 12 H), 5. 08 (s, 2H), 5. 44 (br s, 2H), 7. 33-7. 42 (m, 6H), 8. 03 (s, 1 H).

References:

WO2004/76412,2004,A2 Location in patent:Page 74